Search results for "butanediacetals"
showing 2 items of 2 documents
Synthesis of the aggregation pheromone of the Colorado potato beetle from its degradation product
2015
Incubation of the Colorado potato beetle aggregation pheromone, (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one, with antennal or leg extracts from this beetle gave 6-methyl-5-hepten-2-one as the major product. This ketone was used as a substrate in a stereoselective synthesis of the pheromone. It was attached to the butanediacetal of glycolic acid with good stereoselectivity and the desired isomer was further enriched by purification of the product of this reaction on silica gel.
Selective isomerization of a trans -butanediacetal derivative of tartaric acid with differentiating substituents at C-2 and C-3
2017
Abstract A trans-disubstituted butanediacetal derivative with two different substituents (ester and thioester) – methyl (2R,3R,5R,6R)-3-ethylsulfanylcarbonyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxylate, was selectively converted to the cis derivative – methyl (2S,3R,5R,6R)-3-ethylsulfanylcarbonyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxylate in high yield on a multigram scale. The product of this reaction offers the possibility for selective modification of one of the substituents, which was demonstrated by Fukuyama reduction of the thioester group.